Top Realtors and Real Estate Agents in Winchester, KY
Rankings based on verified MLS transaction data. Last updated May 2026. No pay-to-play.
Top Agent
Top 1.6%
in Winchester, KY
$42.9M
All-Time Sales
$140K - $650K
Price Range
6%
Negotiated Off List
Top AgentTop 2.4%
in Winchester, KY
$161.2M
All-Time Sales
$240K - $1.4M
Price Range
5%
Negotiated Off List
Top AgentTop 2.8%
in Winchester, KY
$434.5M
All-Time Sales
$190K - $2.2M
Price Range
7%
Negotiated Off List
Top Agent
(151)
Terra Long
Keller Williams Greater Lexington
9 Years of experience
44+ Sales in the last 12 months
Top 3.6%
in Winchester, KY
$157.2M
All-Time Sales
$200K - $1.1M
Price Range
4%
Negotiated Off List
Top AgentTop 4.8%
in Winchester, KY
$16.5M
All-Time Sales
$160K - $780K
Price Range
Top AgentTop 9.2%
in Winchester, KY
$50.9M
All-Time Sales
$180K - $1.9M
Price Range
5%
Negotiated Off List
Top AgentTop 10%
in Winchester, KY
$231.1M
All-Time Sales
$170K - $2.3M
Price Range
8%
Negotiated Off List
Top Agent(15)
Jon Bentley
Keller Williams Realty Greater Lexington
7 Years of experience
24+ Sales in the last 12 months
Top 10.8%
in Winchester, KY
$30.5M
All-Time Sales
$220K - $580K
Price Range
4%
Negotiated Off List
Top AgentTop 11.2%
in Winchester, KY
$167M
All-Time Sales
$210K - $2.3M
Price Range
4%
Negotiated Off List
Top AgentTop 13.2%
in Winchester, KY
$111.4M
All-Time Sales
$290K - $1.1M
Price Range
4%
Negotiated Off List
Top Agent(51)
Daphne Jewell
Berkshire Hathaway Home Services
14 Years of experience
18+ Sales in the last 12 months
Top 13.6%
in Winchester, KY
$101.8M
All-Time Sales
$170K - $650K
Price Range
5%
Negotiated Off List
Top AgentTop 14.4%
in Winchester, KY
$25.9M
All-Time Sales
$90K - $940K
Price Range
Top AgentReviews not yet available
Christina Boice
Plum Tree Realty
5 Years of experience
0+ Sales in the last 12 months
Top 18%
in Winchester, KY
$6.3M
All-Time Sales
$170K - $400K
Price Range
2%
Negotiated Off List
Top AgentTop 18.4%
in Winchester, KY
$90.1M
All-Time Sales
$300K - $4.3M
Price Range
Top Agent(6)
Brittany Clark
Century 21 Simpson & Associates
9 Years of experience
26+ Sales in the last 12 months
Top 20%
in Winchester, KY
$27.5M
All-Time Sales
$200K - $1.4M
Price Range
Winchester Housing Market Trends
Median Sale Price
$222,400
+5.90% year-over-yearMedian Days on Market
43
+13 days year-over-yearSale-to-List Price
98.49%
-2.86% year-over-yearHomes Sold Above List Price
12.5%
-3.5% year-over-yearOff the Market in 2 Weeks
47.8%
+17.8% year-over-yearListings With Price Drops
28.7%
-7.6% year-over-yearMonths of Supply
3.3
Realtors in Winchester
250
Verified MLS market data through May 2026.
Do Top Winchester Agents Sell Faster?
The 15 top-ranked agents on EffectiveAgents in Winchester sell in a median of 32 days, compared with the Winchester market median of 43 days on market.
About 11 days faster (26% quicker than the Winchester market)
Median days to sale reported by the top-ranked Winchester agents on EffectiveAgents, compared with the Winchester market median days on market. Agent figures reflect each agent's reported sales history.
When Is the Best Time to Sell a House in Winchester?
Based on the last 24 months of verified MLS market data, homes in Winchester sell fastest and closest to asking when they go under contract in May. To hit that window, plan to list around April.
Median days on market by month (shorter is faster)
May
Best month to sell
37 days
Typical time on market
99.9%
Of asking price
Seasonal averages from the last 24 months of Winchester, KY sales. Individual results vary with price, condition, and how the broader market moves. A local agent can pinpoint the right timing for your home.
How We Rank Winchester Real Estate Agents
Our rankings are built from verified MLS transaction data, not advertising spend. For every agent we analyze more than fifteen performance signals, including sales volume in your city and zip code, recent and all-time transactions, days on market, negotiation results (how far above or below list price an agent's clients actually close), price-point fit, and verified reviews. The agents shown first are those whose verified results put them at the top of the Winchester market today.
Agents cannot pay for placement in these rankings. The underlying data refreshes as new closed transactions are reported, so rankings shift with real market performance. Learn how we rank agents.
Rankings reviewed by Kevin Stuteville, Licensed Florida Real Estate Broker (License BK3068131), Founder of EffectiveAgents.
Data last updated: May 2026
Winchester Real Estate Agent FAQs
How were these Winchester real estate agents ranked?
Rankings are built from verified MLS transaction data. We analyze more than fifteen performance signals for every agent, including sales volume in your city and zip code, recent and all-time transactions, days on market, negotiation results, price-point fit, and verified reviews. Agents cannot pay for placement.
How many real estate agents are in Winchester?
Our data covers 250 real estate agents serving the Winchester area. The count represents agents with transaction activity recorded in our Winchester market data, not simply everyone holding a license.
What does the median sale price in Winchester mean for sellers?
Winchester's median sale price is $222,400 as of May 2026. Half of recent sales closed above that figure and half below. It is a useful baseline for understanding the market, but an experienced local agent will price your home against comparable recent sales in your neighborhood, not the citywide median.
Does it cost anything to use EffectiveAgents?
No. EffectiveAgents is free for home buyers and sellers, with no obligation to work with any agent we match you with.
Do agents pay to be ranked or featured?
No. Agents cannot pay for placement anywhere in these rankings. Positions are earned from verified transaction performance only.
What commission do Winchester realtors charge?
Commissions are negotiable and vary by agent, service level, and transaction. There is no set rate, and recent industry changes have made commission structures more flexible than ever. Discuss the structure directly with your agent before signing a listing or buyer agreement.
Should I use a local Winchester agent or a national brand?
The individual agent matters more than the brand on the sign. Offices within the same national franchise vary widely in performance, and the agent you hire, not the logo, prices your home, negotiates your contract, and manages your closing. A strong local agent brings firsthand knowledge of Winchester neighborhoods, pricing patterns, and buyer activity. Compare agents on verified local results such as recent sales, days on market, and negotiation outcomes rather than name recognition.
What questions should I ask a Winchester realtor before hiring them?
Ask how many homes they have closed in Winchester in the past year, what their average sale-to-list ratio is, and how much of their business is in your neighborhood and price range. Ask how they will market your home or find you listings, and how often they will communicate. Strong agents answer with specifics. Verified transaction data is the fastest way to confirm what you hear.
Top Realtors by Zip Code in Winchester, KY
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